1-Bromooctane → 1-Bromo-4-(4-octoxyphenyl)benzene

HRID 1769569Notes

Reaction equation

HRID 1769569 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CCC(C)=O>[CH2:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 28017871-Bromo-4-(4-octoxyphenyl)benzeneYield 90%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel was charged with 15 g of 4-hydroxy-4'-bromobiphenyl, 14 g of octyl bromide, 16 g of potassium carbonate and 100 ml of MEK, and the mixture was refluxed with stirring for 8 hours (the disappearance of the starting materials was confirmed by GLC). The reaction liquid was filtered to remove solids. The filtrate was concentrated and the residue was recrystallized from acetone to obtain 18 g (90%) of 4-octyloxy-4'-bromobiphenyl.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. customto remove solids
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-be8a7af7debb4321a992cc385dfccc3f
Source dataset
uspto-grants-1995_01
Patent number
US05382380

Reaction notes

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